Much is made of the inextricable link between trust and love, but the assumption seems to be that you can’t love someone else unless you can trust them (to listen, keep it in their pants, rescue you from a sinking ship, etc.). Just as important, however, is the ability to trust yourself and your own judgment when entering into a relationship; if you have too little confidence, you can sabotage your relationships, and if you have too much, you’ll make commitments that won’t last and will hurt like hell when they break down. Learn to trust yourself by gathering facts, observing carefully, and using common sense to judge your friendships and make smart decisions. Then, regardless of over or under-confidence, you’ll be able to love someone you trust and have trust in whom you love.
–Dr. Lastname

I am in a good relationship and have been now for a while (around 9 months). But none of my relationships seem to last more than a couple of years (I’m now in my 40s), and I worry that some of them I have sabotaged myself. I am at a point in this relationship where we have acknowledged that we love each other and have started making plans months into the future (nothing like moving in together, but definitely trips and such), and suddenly, I have this fear I’m going to lose him. But not just lose him—lose him to someone, and that someone is my friend. I had a friend when I was younger that flirted with my boyfriends, and even though nothing ever happened, it bothered me that she never understood these boundaries, didn’t have a sense of loyalty towards me, and used her looks and sexuality to get attention from those that should be considered off limits. Now I have a newer friend who is younger than me—she’s very pretty, smart, and single, and she has a tendency to try to connect with my boyfriend in ways that I am unable to by finding the gaps and honing in and I don’t like it. I am acting as though they have already run away together, or have a secret relationship. Is my own insecurity causing me to worry about this? My goal is to alleviate these fears of betrayal.

Having fun friends with fickle boundaries may damage your calm, but you do yourself more damage by letting them distract you from the real issues surrounding your boyfriend and your future together. Instead of worrying about whether your gal pals have good intentions, focus on doing the necessary homework to find out whether your boyfriend is a good match.

Assuming you’re not able to stop yourself from being insecure about your friends and boyfriends, use your insecurity to assess your boyfriend’s trustworthiness. Maybe you can also use it to get better at screening friends in the future, but for now, believe it or not, your best weapon against your paranoia is paranoia itself.

Instead of trying to feel better by talking about your fears and asking for reassurance, use them to review your boyfriend’s history with women and your girlfriend’s history as a femme fatale. Your anxiety will drive you to ask the right questions, and, with any luck, the right answers will allow you to tell that anxiety to shut up.

First, ask yourself why your boyfriend isn’t married at the age of 40 or thereabouts. If it’s because he had long-term relationships with women who dumped him or were absolutely impossible, then you’ve got good reason to believe he has a capacity for commitment and isn’t fickle—he just has a thing for difficult women. If he’s been afraid of commitment, on the other hand, then you have to wonder whether he’ll ever move forward.

If he’s a reasonable partnership candidate, ask yourself what you want to do with him and whether it includes kids. If you want marriage, and particularly kids, it’s time to get moving and let him know of your intentions. Don’t let anxiety get you to be passive and avoid important questions.

In the meantime, don’t socialize with him and your single girlfriends at the same time; it’s not that difficult to arrange, and it’ll give you a chance to find things the two of you like to do together. It’s also important to find out if you two can spend low-key, near-boring time together doing nothing, as normal couples do. This is your time to build a working relationship, not test his loyalty and sexual attention span. If there’s reason to doubt his fidelity, dump him and count yourself lucky. If there isn’t, don’t let your fears or your friends get in the way of your goals.

Do careful screening and see if you can build a good working relationship that can survive boredom, work, and flirty friends. If it can, get moving, close the deal, and enjoy a nice, boring relationship, maybe with some new boring friends on the side.

STATEMENT:
“I feel like my friend is so good at appealing to my boyfriend that she will steal him away, but if it’s that easy, I don’t want him. The bigger danger, in all probability, is that he’s not a good candidate or that we’re both too anxious to move forward. Regardless of my doubts, I will do the research, make my decision, and not let anxiety slow me down.”

The shrinks at the hospital diagnosed my brother bipolar, but he’s sure he’s fine without medication, and most of the time he’s able to hold a job without sounding nuts or making bad decisions. In his personal life, though, he has a tendency to fall in love with trashy women he’s known for maybe 10 minutes, and after 11 minutes he’s ready to introduce them to the family. Of course, when I tell him I’m worried about his choices, he gets angry, and then my father tells me I’m undermining his confidence, which makes me angry. My goal is simply to protect him from his bad, bipolar taste in women as crazy as he is.

The key to talking with someone about their dating choices is to take that personal topic to the most impersonal level possible; it’s not about whom they’re dating, but how they’d like to date, period. Instead of sharing your feelings about the character of your brother’s new love or whether or not you like her, invite him to share his hopes, dreams, and dating methods. Otherwise, regardless of your good intentions and the fact that he asked you to be honest, your honest feelings will trigger his, and he has feelings to spare.

You don’t have to lie about your feelings in order to keep them to yourself, you just need to refocus the conversation. He may even want to know how you feel about his new love and ask you directly, but your response, if you want to be helpful and avoid a shit-fest, is that you don’t really know her and don’t have an opinion at this early stage of their relationship. It’s the least-provocative, most-honest answer in your arsenal.

Bypass his excited account of how thrilling it was to meet her and how much they enjoy one another’s company, and instead ask him whether his past dating experiences have ended painfully or not and whether he wants to get married and have kids. Make it clear that you don’t want to judge whether his current girlfriend will break his heart or be a bad mother; you just want to know whether those are important issues for him and, if so, how he protects himself.

Of course, if he’s not vulnerable to loss or refuses to plan his future, your conversation will not get off the ground. You’ll know you’ve tried, however, while protecting yourself from an ugly conversation about your unwillingness to appreciate his girlfriend or let him, just this once, be happy.

No matter what you say, you can’t fully protect him from his illness or feeling-driven dating practices; all you can do is offer him tools for deciding for himself whether he needs protection. Unfortunately, illness and/or stubbornness can make it impossible for him to see what you mean.

Don’t back away from your view, however, that long-range thinking about the goals and risks of a relationship is worth doing, and that you’re always available to help. Then, when trouble develops, tell him he can prevent it in future if he thinks more about his methods, and then brace yourself the next love of his life (and all the ones after that).

STATEMENT:
“I can’t stand to see my brother dating girls who are likely to break his heart or give him a family he’s not ready for, but I doubt he has control over his decisions and I certainly don’t. I will avoid go-nowhere arguments about trashiness and instead try to persuade him that there are decision-making techniques he should use in addition to intuition and instinct.”